Nitric Acid → 3-acetyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 1668578Notes

Reaction equation

HRID 1668578 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)(=[O:7])[CH3:6].[OH-].[Na+]>>[C:5]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][C:17]([N+:1]([O-:4])=[O:2])=[CH:18][C:11]=2[CH2:10][CH2:9]1)(=[O:7])[CH3:6]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 193754873-acetyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 218229223-acetyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Procedure

To a cooled solution of HNO3 (70%) at 10° C., 3-acetyl-2,3,4,5-tetrahydro-1H-3-benzazepine (6.8 g, preparation reported in WO 02/40471) was added portionwise over 20 min. After addition mixture was allowed to warm at rt. and stirred for further 4 h. Mixture was poured into ice and pH adjusted to 11 using NaOH (conc) then was extracted with DCM. The organic layer was collected and the aqueous phase extracted twice with DCM. The combined DCM layers were concentrated to provide the target compound (7.74 g), which was used in further conversions without any purification.

Workup

  1. additionAfter addition mixture
  2. additionMixture was poured into ice
  3. extractionthen was extracted with DCM
  4. customThe organic layer was collected
  5. extractionthe aqueous phase extracted twice with DCM
  6. concentrationThe combined DCM layers were concentrated

Sources & evidence

ORD record
ord-8c091477cdf54a20b3b0caa7f99de950
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

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